My Boss Is A Sissy Boy free porn video

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I was a wrestling athlete at schooldays, 8'00" tall and 180 lb now 45 y/o, was good at sports at schooldays but week at job of at our company ,not yet am boss.I am Ryuzoh Sejima,call me Ryu.
At the beginning of this year,new boss came to our team of the company.He is Kaoru Tachibana, 25 y/o about 5'6",under 150 lb,looks like a sissy boy with a girly round butt. Indeed he is a good reader, clever and wise from a famous college.I respect him as a boss but I become horny when I look at his butt in spit of wearing.
One day a staff of the general affairs division said me to teach him the new staffs body size for making new uniforms. I thought it is good chance.
"Excuse me,my boss.I must research the body size of new staffs of our division.I want you to teach me your body size."
"Mr. Ryu, I don't know my collect size,sorry.Is it nude size?"
"Yes,nude size."
"Oh,I can't measure collect size of my own body size.Measure me,would you?"
"Yes! Oh,yes sir,my boss!Go to the locker room together !"
We went to the locker room and rock the key of the door for nude body.
"By the way, Ryu. I am too shy to be full nude in front of a crossing man. "
"I have an idea,boss.We to men will take all clothes off to be full nude,OK? "
"Oh,nice idea!Ryu, at first,you make yourself naked to be a nude body."
"Yes,sir,my boss!"
I did and my 10 inch cock appeared,and he surprised at it and said
"Oh,you have a very big cock,yours is twice size of mine."
"Really?I want to see your cock, maybe a pretty cock."
"Yes,I show you my pretty one."
I surprised that he didn't feel a sense of inferiority about cock size.
And surprised that He took off his pants,shirt,tank-top.And next time I surprised that he was wearing panties for women.He noticed my surprised face and said
"Ryu,I am a crossdresser while at home."
"I see,it's OK,my boss.But your ass is very big and round just like a woman!"
"Thank you"said and pull down panties, his sexy naked ass appeared!
"Ryu,measure me!"
I measured his chest, waist and hip,oh,I could touch his ass and feel his soft cheek of ass.
"My boss, you looks like just a girl,which man or woman do you fuck with?"0
"I have no answer,because I am a cherry boy yet! But I am a man not a woman,I think I can't fuck with a man,because I don't have a pussy,you say funny thing!!"
"Yes,indeed you don't have a pussy hole,but just have a anal hole! You can receive a male cock with your anal hole!!"
"I didn't notice such a way! But don't you think anal hole is dirty? "
"No problem! If you have an enema hobbit, you can keep your ass pussy more cleaner than female pussy, hahaha!! "
"But comfortable ?"
"Anal hole and pussy hole are almost same. Don't you think it's unfair if only women could enjoy hole comfort."
"Off course it's unfair! but I have no lover who fuck my ass pussy!"
"In fact I respect you as a boss, but as a boy, I love you,and your girly round ass !"
"Off course I respect you as a good staff too, I'm glad that treat my ass tenderly as a lover,my daddy!! "
Ryu holed a body of his young boss and kiss with his tongue inserting young boy's tongue,tow tongues stared to lick together!

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You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

2 years ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

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